Arnold Rothstein: New York’s First Criminal Genius

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Damon Runyon dubbed him “The Brain.”

To F. Scott Fitzgerald he was the vulgarian Meyer Wolfsheim. To the sports, grifters, gyps, and conmen who wanted to work with him, he was “the Big Bankroll” or “the Big Jew Uptown.” To those who knew him well, he was A. R.—Arnold Rothstein.

Born the second son of a prosperous, devout Jewish family in 1882, he rebelled against everything his father tried to teach him, particularly gambling. It was simply forbidden and that made it even more seductive to the young man. He had an innate understanding of numbers combined with competitive fire. Games like pool, poker and dice came easily to him. As a young man he was slim, athletic, and quick; about 5’7” or 8” with dark hair and a clear pale complexion. He always wore the expensive, well-tailored clothes of a gentleman. Nothing flashy No jewelry save perhaps a tasteful diamond stickpin. Didn’t smoke, didn’t drink, didn’t chew. Tobacco or gum.

Soft-spoken unless he needed to be overheard.

During his eventful life, Rothstein was involved in so many things—bootleg alcohol, drugs, gambling, theft, real estate, union-busting, bribery, loan-sharking—with so many people that it’s impossible to say whether any story about him is completely true or even mostly true. After he died, just about everybody who had dealings with him had something to say. Most of them didn’t like him, for all the right reasons, and inevitably they made themselves look good. Or at least not completely guilty. How much is true, exaggerated, outright invention? Who can say?

The man was brought up on charges more than once. Never convicted. He was able to break the law so openly because he was deeply connected to every part of New York society—government, the financial world, show business, Broadway, the muckety-mucks, and the mobsters.

He was famous for carrying fat wads of cash on his person. If you happened to have an opportunity to invest in a dicey enterprise that banks and other lenders wouldn’t touch, you might be able to persuade Mr. Rothstein to loan you the cash. The interest would be steep, and you might have to take out one of his life insurance policies. Then if you didn’t pay it back, Abe Attell, Fats Walsh and the legendarily brutal Monk Eastman would work you over. But those were risks you take. If A. R. thought your idea might pay off, he would offer to invest. If he offered, you agreed.

He said that he never gambled against a man he didn’t know he could beat, and he took a joy in besting those who presumed to be his social betters. Toward the end, that desire to win curdled into self-destruction. Perhaps he made so much money, found so much fame, had so many women, and owned so many things that none of it meant anything to him. Then what was left?

When he first tried to make a living as a gambler, he was moderately and sporadically successful. He soon realized that the only sure way to make it was to own the establishment. He began to earn a name for himself in 1909 after he won an ultra-marathon 32-hour pool match against a young gent said to be the best amateur “billiardist” in America. Also in 1909, he married actress and showgirl Carolyn Green in Saratoga, New York where he would soon open a casino. (In those years anybody who was anybody in New York spent August up in Saratoga Springs at the races and enjoying the other entertainments that the town offered.)

A. R. opened his first casino on West 46^th St. with protection paid to Tammany Hall boss Big Jim Sullivan. (Years earlier, Tammany had been described as “that lying, perjured, rum-soaked, libidinous lot” and it hadn’t gotten any better.) Before long, his place was one of the most popular and profitable gambling houses in the city. Later, when reformers managed to shut down casinos, he created “floating” crap games, immortalized in Guys and Dolls, that moved from place to place. During that time, Rothstein’s power grew as he became a sought-after fixer and middleman for dealings among crooked politicians, crooked cops, and crooks. In that capacity he gained considerably more influence.

Climbing the social ladder, he owned racehorse stables and tracks. He opened another casino in Sarasota Springs, The Brook, one of the snazziest in the country. Like the other gambling establishments there, it was completely illegal. He paid local politicians $70,000 to keep it open.

(Read these dollar amounts with some skepticism. They’re guesses, approximations, and exaggerations made by A. R.’s contemporaries and the writers who came before me. But if they’re not completely accurate, it’s safe to say that Arnold Rothstein made and lost a lot of money in the first decades of the 20^th century. He was at or near the center of most criminal activity in the city, the more profitable parts, anyway.)

He is said to have earned as much as $5,000,000 stealing Liberty Bonds, meant to fund America’s efforts in World War I. These were Bearer Bonds that could be redeemed by anyone who had them. A. R. and gambler “Nicky” Arnstein (Mr. Fanny Brice) struck a deal to steal them from cooperative messengers who agreed to be robbed for a price. Rothstein got into labor racketeering by promising loans to the Communist Party and facilitating their bribes to the right judges and cops.

Any doubts about A. R.’s power were put to rest in January, 1919, when one of his dice games in a fourth-floor apartment was raided by the cops. About twenty gamblers were in attendance when a man pounded on the door and yelled for those inside to open up.

Untypically, A. R. pulled a pistol and fired through the door before it burst open, and eight officers charged through. They were led by Inspector Dominic Henry. Rothstein had hit and slightly wounded three detectives—John McLaughlin, John J. Walsh, and Dick Oliver.

“Where’s Rothstein?” one of them yelled, letting the assembled sportsmen know that someone had ratted the Bankroll out.

But Rothstein was nowhere to be found in the crowded apartment after it had been searched. As the detectives herded their charges downstairs into a waiting paddy wagon, a helpful bystander told them that he had seen a man on the second-floor fire escape. A. R. was escorted to the street where he was horrified to learn that McLaughlin and Walsh had been injured. Rather than wait for an ambulance, he suggested that the detectives take his limousine to the hospital. It’s the Rolls right over there.

A little later that night, Magistrate Francis X. Mancuso ordered $1,000 bail for each of the players. Rothstein ponied up for all of them with a roll of thousands in his pocket. The whole unfortunate affair was almost swept under the carpet right there. The officers were not seriously wounded; perhaps, they admitted, they hadn’t properly identified themselves, and besides, A. R. had a pistol permit. Still, Rothstein thought it wise to retain Bill “The Great Mouthpiece” Fallon and former Magistrate Emil Fuchs to represent him.

In February, a grand jury was convened by D.A. Edward Swann to investigate. All of the gamblers were called to testify, but nobody who’d been there could remember anything. Only one guy even recalled a shot being fired and he couldn’t say who did it. No one was charged but Rothstein. When he was brought before a judge in June, those charges were dismissed forthwith, proving once again that New York has the best legal system money can buy.

He became nationally infamous for his involvement with the 1919 “Black Sox” World Series but the truth of his part in that complex multifaceted conspiracy will never be known. It’s fair to say that he made money on it, and that he provided backing for part of it. Beyond that, there are dozens of variations.

Sometime that summer he learned that several Chicago White Sox players were interested taking money to lose. They were prohibitive favorites over the Cincinnati Reds, but one story has it that they were already known as the “Black Sox” because their owner Charles Comiskey was such a tightwad. He didn’t pay his players what they deserved and he wouldn’t even pay to launder their uniforms. An unhappy bunch they were. For the right offer, some of them were ready to sell out. Several sportsmen, including former big-league pitcher Sleepy Bill Burns, were eager to facilitate those efforts. One night in September, Burns and two other men approached A. R. in the dining room of the Hotel Astor and asked him for financing. Rothstein told the men that he wanted no part of their scheme. It wouldn’t work… why were they bothering him… he would never…

He deliberately spoke loudly in front of many witnesses who would remember the moment years later when it was time to testify.

Actually, Rothstein was already involved to some degree in another effort or efforts to put in the fix. Several schemes were in play. Other writers who have examined that scandal in depth give A. R. different levels of involvement. Whether he was the prime instigator or not is relatively unimportant. A year later, when he was called before a Chicago grand jury, Rothstein denied any involvement and mentioned that night at the Astor. He was not indicted. When the scandal was brought to trial two years later in 1921, it was another triumph for American justice. Evidence and signed confessions were “lost.” Sleepy Bill turned state’s evidence and testified that Rothstein had been in on it. No matter. He wasn’t even charged and the players were declared not guilty. Banned from baseball, yes, but not guilty in the eyes of the law.

But Rothstein’s most enduring contribution to American crime came when he realized before anyone else what Prohibition was going to be like and the opportunities it presented. Again, there are several variations on this story involving different young and ambitious gangsters. Here are the basics:

Understanding that people in New York weren’t going to stop drinking just because a bunch of rural moralists declared that booze was illegal, A. R. went to Scotland and England and made deposits with the distillers he knew. He bought as much of their product as he could while it was still in the barrel. He also made arrangements to have the hooch shipped to America in freighters.

But to actually sell the stuff, he had to get it ashore and distribute it. That was going to be a massive operation. To do it, he needed partners—young, smart, energetic partners. Enter 18-year-old Meyer Lansky. A. R. invited him to a private dinner at the Park Central Hotel. For six hours, he flattered the young man and told him the details of his proposed operation. His ships would anchor just outside of the three-mile limit off Long Island and New Jersey. Speedboats would bring the alcohol on shore, and then trucks and cars would transport it to warehouses. Along the way, bribes would be handed out as needed to law enforcement.

By the end of the meeting Lansky had agreed to join him and to bring in his friends Charlie Lucania (soon to rename himself Luciano), Abner “Longie” Zwillman who ran things across the river on the Jersey side, and a few others.

Lansky’s relationship with Luciano was central to Rothstein’s plans. At the time, “Charlie Lucky” was one of the few Italian mobsters who would work with Jews. He and Meyer had been close for years and A. R. knew the two made a formidable partnership. Luciano had the personal charm and society connections to operate outside the Italian neighborhoods. Lansky had the maturity—even then—and brilliant business sense to guide their operations, tempering his friend’s more impulsive side.

 

Rothstein did not stay in the rum running business for long. It grew so quickly and became so large that no single individual could come close to controlling it. But he could use his European connections for other illegal enterprises, namely narcotics. But they were different. True, there weren’t as many drug users as tipplers but many of them became addicts. Also, the logistics of moving smaller amounts of pure pharmaceuticals from Merck, Bayer and the like in Europe were much more manageable.

In the later years of his life, Rothstein’s life slowly fell apart. By then, his primary source of income was drugs, though he always denied it. When questioned, he would answer that yes, he loaned money to people who imported drugs but he never ordered them to do it. Baloney.

In 1927 his mistress, showgirl Bobbie Winthrop, committed suicide and his wife Carolyn filed for divorce. His luck or his inside information at the track deserted him. On Memorial Day, 1928, he dropped $130,000 at the Belmont racetrack. Other gambling became compulsive and one complex and expensive real estate deal ground to a halt without profits. The Broadway show people and businessmen no longer wanted to be seen with him.

In September, 1928, he got into a big poker and crap game hosted by George “Hump” McManus. It began on a Saturday night and didn’t end until Monday morning. A. R. lost more than $300,000 to men who knew him and didn’t like him. Those losses were in markers—I.O.U.s—not cash. On the way out the door, he claimed he’d been cheated and so he wasn’t going to pay. What! Rothstein welshing on a bet? Word of that inexcusable behavior got about quickly but A. R. claimed to be unafraid. If they tried to kill him, he rationalized, they’d never get their money.

On the night of November 4, McManus called Rothstein at Lindy’s deli, where he conducted business. A. R. agreed to meet him at the Park Central Hotel alone and unarmed. On the way out of Lindy’s he gave his pistol to Jimmy Meehan, a small-time gambler who’d been involved in the big game. In Room 349 of the Park Central somebody plugged him in the belly with a .38. The bullet ruptured his bladder and damaged his intestines, causing terrible internal bleeding. A. R. made his way down a service staircase to the street and demanded to be taken to the Polyclinic Hospital. He wanted his own doctor. He also asked a police officer on the scene to call his lawyer. “Tell him to bring down the will.”

At 3:50 the next morning, the lawyer did appear with a new unsigned will, which he claimed A. R. had made the day before. He put a pen in the dying man’s hand and guided it across the paper in a faint “X.” Rothstein died at 10:50 without naming his killer. (The new will angered just about everyone it mentioned.)

Some sources say McManus pulled the trigger and a strong circumstantial case can be made against him. He was acquitted in a farcical trial. Others pin A. R.’s death on his ex-bodyguard Legs Diamond. Like his role in the 1919 Series, the whole truth will never be known.

In his time, Arnold Rothstein became powerful because he knew how to exploit weakness. He learned how to profit off the corruption that surrounded him. In most situations, he calculated the odds unemotionally after convincing himself that his superior knowledge gave him an edge. For a long time, it did.

Meyer Lansky put it this way: “The gambling fever that was always part of Arnie’s make-up appeared to have gone to his brain. It was like a disease and he was now it its last stages. He gambled wildly.”

“Wild” gamblers do not win. Nobody knew that better than Arnold Rothstein.

Sources:

The Betrayal. Charles Fountain. 2016

Blood and Power. Stephen Fox. 1989.

Eight Men Out. Eliot Asinof. 1963

“Founding Father.” Jill Jonnes. American Heritage magazine. Feb/Mar. 1993, vol. 44, No.1.

Gangsters and Gold Diggers. Jerome Charyn. 2003.

Hep-Cats, Narcs and Pipe Dreams. Jill Jonnes. 1996

The Last Testament of Lucky Luciano. Martin A. Gosch & Richard Hammer. 1974.

Little Man. Robert Lacey. 1991.

Madam. Debby Applegate. 2021.

Meyer Lansky, Mogul of the Mob. Dennis Eisenberg. 1979.

Rothstein. David Pietrusza. 2003.

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